Look at him now: Chris Brown winning as rapper

FILE - In this July 15, 2011 file photo, singer Chris Brown performs on NBC's Today Show in New York. With his hit single â€œLook at Me Now,â€ Brown has dominated more than just the R&B territory: The track was Billboard's No. 1 rap song of 2011 and it's nominated for two Grammys _ in the rap category.

NEW YORK — Chris Brown is known pop singer, a slick bedroom crooner and at other times, a Euro-flavored dance singer. But it's his rapping that has taken his career to new heights.

With his hit single "Look at Me Now," Brown has dominated more than just the R&B territory: The boastful track, which co-stars Lil Wayne and Busta Rhymes, was Billboard's No. 1 rap song of 2011 and it's nominated for best rap song and best rap performance at Sunday's Grammy Awards, where Brown's competition includes Jay-Z, Kanye West, Dr. Dre and Eminem.

The song is just another example of Brown's rapping prowess. At last year's BET Hip-Hop Awards, Brown went toe-to-toe with other hip-hop acts during one segment, and was so strong he left 50 Cent wowed.

"Chris particularly was impressive," said 50 Cent. "He rapped better than the rappers. I'm going to give it up. I'm watching the show (like), 'How did they let that happen?'"

50 Cent is not the only member of the hip-hop community impressed by Brown: "(Chris) did a mixtape that really blew my mind and I didn't know that was him rhyming," said Questlove of The Roots.

But Brown isn't the only singer who has ventured out to rhyming: Usher rapped on his 1998 hit "My Way" and Trey Songz has released rap mixtapes. Others who have spit a few bars in song include Justin Timberlake, Ne-Yo, Monica, Erykah Badu, R. Kelly, Janelle Monae, Jill Scott, Tyrese, Chrisette Michele and Miguel.

English-based R&B singer Marsha Ambrosius said her first-ever single featured her rapping under the name Ms. Parker, and Brandy — as her alter-ego Bran' Nu — rapped on two songs from Timbaland's "Shock Value II" album, and even had plans to release a rap album before she scrapped the project.

Mary J. Blige also has a rap alter-ego: Brook Lynn. Brook Lynn first appeared on Blige's 2005 album "The Breakthrough." Blige says she's not sure other singers will find success as rappers, though.

"I don't know if it will translate to what a real hip-hop artist would do like 50 (Cent) or Jay-Z or Common or Kanye," Blige said.

But rappers have had luck with singing over the years, from Nelly to Ja Rule. West used the Auto-Tune on most of his "808s & Heartbreak" album, to mixed critical and commercial success. And Nicki Minaj's latest hit — the David Guetta song "Turn Me On" — features the animated rapper belting semi-high notes.

There are also acts like Lauryn Hill, Drake and Missy Elliott — arguably the most respected singer-rappers in the game — who are often praised for blending the two.

"I think you have to come out as a hybrid," said rapper J. Cole, who sings his own hook on the song "Work Out."

"(With) Drake, some people look at him as a rapper who sings, some people look at him as a singer who raps, but he came out that way so nobody's really right or wrong, and he can win forever in either world," Cole continued.

Brown's "Look at Me Now" spent eight and 10 weeks at the top spot on Billboard's R&B/Hip-Hop and Rap songs charts, respectively. Mark Pitts, the president of urban music at RCA Music Group who signed Brown to Sony at age 16, said he initially didn't want to see the singer rapping.

"It took me a minute to really appreciate ('Look at Me Now'). I didn't want to like it because I didn't want him rapping," Pitts said.

Rapping is a departure for 22-year-old Brown, who debuted on the scene in 2005 as an R&B-pop heartthrob. Pitts said that past Brown songs where a rapper is featured most likely had a rap verse from Brown first, but they were never used. Pitts, who has overseen the careers of the Notorious B.I.G., Diddy and Usher, says he once thought singers and rappers should stay in their own lanes.

But Brown helped change his perception.

"It's a different age now," Pitts said. "I'm not surprised by anything from (Chris) anymore. He's not in one category. It works for him, and not everybody can do that."

Brown's CD where "Look at Me Now" appears — "F.A.M.E. (Forgiving All My Enemies)" — is nominated for best R&B album at the Grammys; his upcoming fifth disc, "Fortune," will most likely feature rapping, Pitts said. Brown has received respect from the rap community, and often appears on hip-hop tracks. But not all singers are poised to have a similar triumph.

"It's definitely difficult for an R&B singer to be accepted as a hip-hop rapper, but I know it's possible," Common said. "If you do it well, it will be accepted."

50 Cent agrees, adding that musicians are often typecast.

"In music there becomes a cut-out of what they'll accept from you and what they won't," he said. "We can take a hit Drake song and I'll deliver it and people will be like, 'Man, get this (expletive) out of here.' They'll be like, 'We want the old 50 (Cent).'"

But Pitts says he's encouraging his newer singing acts to rap.

"It doesn't really bother me (any) more. It used to bother me. But why fight it? If it sounds good, it sounds good," he said. "As long as you're not trying to be someone else, I'm cool with it."